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Erschienen in: Journal of Polymer Research 12/2017

01.11.2017 | ORIGINAL PAPER

Novel hybrid block copolymer nanocarrier systems to load lipophilic drugs prepared by microphase inversion method

verfasst von: Andrea Granada, Issei Otsuka, Thiago Caon, Marcos Antonio Segatto Silva, Valdir Soldi, Redouane Borsali

Erschienen in: Journal of Polymer Research | Ausgabe 12/2017

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Abstract

Nanoparticles based on block copolymers of oligosaccharides [β-cyclodextrin (βCyD) and maltoheptaose (Mal7)] and poly(ε-caprolactone) (PCL) were prepared by microphase inversion method. Zeta-potential, particle size measurements and morphological analysis of drug-free and drug-loaded nanoparticles were performed by using, respectively, laser-doppler anemometry, dynamic and static light scattering and transmission electron microscopy. ρ-Ratio values were correlated with transmission electron microscopy observations. Both types of amphiphilic block copolymers, βCyD-b-PCL5k and Mal7-b-PCL5k, self-assembled in water to form spherical vesicles, presented a hydrodynamic diameter of 72 and 34 nm, respectively. The incorporation of drugs into nanoparticles did not affect significantly the particle size for βCyD-b-PCL5k-based nanoparticles with progesterone, unlike the other tested systems. On the other hand, all nanoparticles (with and without drug) were negatively charged. Both nanoparticulate systems showed high drug loading efficiency (higher than 95%), confirming their suitability as delivery system for lipophilic drugs.

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Literatur
1.
Zurück zum Zitat Aachmann FL, Otzen DE, Larsen KL, Wimmer R (2003) Structural background of cyclodextrin-protein interactions. Protein Eng 16(12):905–912CrossRef Aachmann FL, Otzen DE, Larsen KL, Wimmer R (2003) Structural background of cyclodextrin-protein interactions. Protein Eng 16(12):905–912CrossRef
2.
Zurück zum Zitat Ammar HO, El-Nahhas SA, Ghorab MM, Salama AH (2012) Chitosan/cyclodextrin nanoparticles as drug delivery system. J Incl Phenom Macrocycl Chem 72(1-2):127–136CrossRef Ammar HO, El-Nahhas SA, Ghorab MM, Salama AH (2012) Chitosan/cyclodextrin nanoparticles as drug delivery system. J Incl Phenom Macrocycl Chem 72(1-2):127–136CrossRef
3.
Zurück zum Zitat Archontaki HA, Vertzoni MV, Athanassiou-Malaki MH (2002) Study on the inclusion complexes of bromazepam with beta- and beta-hydroxypropyl-cyclodextrins. J Pharm Biomed Anal 28(3-4):761–769CrossRef Archontaki HA, Vertzoni MV, Athanassiou-Malaki MH (2002) Study on the inclusion complexes of bromazepam with beta- and beta-hydroxypropyl-cyclodextrins. J Pharm Biomed Anal 28(3-4):761–769CrossRef
4.
Zurück zum Zitat Bettinettii GR, Mura R, Melani F, Rillosi M, Giordano F (1996) Interactions Between Naproxen and Maltoheptaose, the Non-Cyclic Analog of β-Cyclodextrin. J Incl Phenom Mol Recognit Chem 25, 327–338 Bettinettii GR, Mura R, Melani F, Rillosi M, Giordano F (1996) Interactions Between Naproxen and Maltoheptaose, the Non-Cyclic Analog of β-Cyclodextrin. J Incl Phenom Mol Recognit Chem 25, 327–338
5.
Zurück zum Zitat Burchard W (2001) Structure formation by polysaccharides in concentrated solution. Biomacromolecules 2(2):342–353CrossRef Burchard W (2001) Structure formation by polysaccharides in concentrated solution. Biomacromolecules 2(2):342–353CrossRef
6.
Zurück zum Zitat Burchard W, Patterson GD (1983) Light scattering from polymers secondary title, vol 48. Springer, Berlin, pp. 1–124CrossRef Burchard W, Patterson GD (1983) Light scattering from polymers secondary title, vol 48. Springer, Berlin, pp. 1–124CrossRef
7.
Zurück zum Zitat Caon T, Porto LC, Granada A, Tagliari MP, Silva MA, Simoes CM, Borsali R, Soldi V (2014) Chitosan-decorated polystyrene-b-poly(acrylic acid) polymersomes as novel carriers for topical delivery of finasteride. Eur J Pharm Sci 52:165–172CrossRef Caon T, Porto LC, Granada A, Tagliari MP, Silva MA, Simoes CM, Borsali R, Soldi V (2014) Chitosan-decorated polystyrene-b-poly(acrylic acid) polymersomes as novel carriers for topical delivery of finasteride. Eur J Pharm Sci 52:165–172CrossRef
8.
Zurück zum Zitat Dalmora ME, Dalmora SL, Oliveira AG (2001) Inclusion complex of piroxicam with beta-cyclodextrin and incorporation in cationic microemulsion. In vitro drug release and in vivo topical anti-inflammatory effect. Int J Pharm 222(1):45–55CrossRef Dalmora ME, Dalmora SL, Oliveira AG (2001) Inclusion complex of piroxicam with beta-cyclodextrin and incorporation in cationic microemulsion. In vitro drug release and in vivo topical anti-inflammatory effect. Int J Pharm 222(1):45–55CrossRef
9.
Zurück zum Zitat Dumitriu S (2001) Polysaccharides as biomaterials. Marcel Dekker, New YorkCrossRef Dumitriu S (2001) Polysaccharides as biomaterials. Marcel Dekker, New YorkCrossRef
10.
Zurück zum Zitat Gomes MJ, Martins S, Ferreira D, Segundo MA, Reis S (2014) Lipid nanoparticles for topical and transdermal application for alopecia treatment: development, physicochemical characterization, and in vitro release and penetration studies. Int J Nanomedicine 9:1231–1242 Gomes MJ, Martins S, Ferreira D, Segundo MA, Reis S (2014) Lipid nanoparticles for topical and transdermal application for alopecia treatment: development, physicochemical characterization, and in vitro release and penetration studies. Int J Nanomedicine 9:1231–1242
11.
Zurück zum Zitat Granada A, Murakami FS, Sartori T, Lemos-Senna E, Silva MA (2008) Development and validation of an HPLC method to quantify camptothecin in polymeric nanocapsule suspensions. J AOAC Int 91(3):551–556 Granada A, Murakami FS, Sartori T, Lemos-Senna E, Silva MA (2008) Development and validation of an HPLC method to quantify camptothecin in polymeric nanocapsule suspensions. J AOAC Int 91(3):551–556
12.
Zurück zum Zitat Granada A, Tagliari MP, Soldi V, Silva MAS, Zanetti-Ramos BG, Fernandes D, Stulzer HK (2013) Nifedipine-loaded polymeric nanocapsules: validation of a stability-indicating HPLC method to evaluate the drug entrapment efficiency and in vitro release profiles. J AOAC Int 96(2):276–281CrossRef Granada A, Tagliari MP, Soldi V, Silva MAS, Zanetti-Ramos BG, Fernandes D, Stulzer HK (2013) Nifedipine-loaded polymeric nanocapsules: validation of a stability-indicating HPLC method to evaluate the drug entrapment efficiency and in vitro release profiles. J AOAC Int 96(2):276–281CrossRef
13.
Zurück zum Zitat Guo Z, Jin Y, Liang T, Liu Y, Xu Q, Liang X, Lei A (2009) Synthesis, chromatographic evaluation and hydrophilic interaction/reversed-phase mixed-mode behavior of a "Click beta-cyclodextrin" stationary phase. J Chromatogr A 1216(2):257–263CrossRef Guo Z, Jin Y, Liang T, Liu Y, Xu Q, Liang X, Lei A (2009) Synthesis, chromatographic evaluation and hydrophilic interaction/reversed-phase mixed-mode behavior of a "Click beta-cyclodextrin" stationary phase. J Chromatogr A 1216(2):257–263CrossRef
14.
Zurück zum Zitat Guo YL, Cui ZS, Han M (2013) Synthesis, micellization and characterization of novel amphiphilic beta-cyclodextrin/poly(L-aspartate) copolymer. Chem Res Chin Univ 29(3):603–606CrossRef Guo YL, Cui ZS, Han M (2013) Synthesis, micellization and characterization of novel amphiphilic beta-cyclodextrin/poly(L-aspartate) copolymer. Chem Res Chin Univ 29(3):603–606CrossRef
15.
Zurück zum Zitat Hansch CLA, Hoekman D, Exploring QSAR (1995) Hydrophobic, electronic and steric constants. American Chemical Society, Washington, DC Hansch CLA, Hoekman D, Exploring QSAR (1995) Hydrophobic, electronic and steric constants. American Chemical Society, Washington, DC
16.
Zurück zum Zitat He Y, Fu P, Shen X, Gao H (2008) Cyclodextrin-based aggregates and characterization by microscopy. Micron 39(5):495–516CrossRef He Y, Fu P, Shen X, Gao H (2008) Cyclodextrin-based aggregates and characterization by microscopy. Micron 39(5):495–516CrossRef
17.
Zurück zum Zitat ICH (2005) International conference on harmonization of technical requeriments for registration of pharmaceuticals for human use: Q2(R1)-validation of analytical procedures: text and methodology. ICH harmonised tripartite guideline ICH (2005) International conference on harmonization of technical requeriments for registration of pharmaceuticals for human use: Q2(R1)-validation of analytical procedures: text and methodology. ICH harmonised tripartite guideline
18.
Zurück zum Zitat Isono T, Otsuka I, Suemasa D, Rochas C, Satoh T, Borsali R, Kakuchi T (2013) Synthesis, self-assembly, and thermal caramelization of maltoheptaose-conjugated polycaprolactones leading to spherical, cylindrical, and lamellar morphologies. Macromolecules 46(22):8932–8940CrossRef Isono T, Otsuka I, Suemasa D, Rochas C, Satoh T, Borsali R, Kakuchi T (2013) Synthesis, self-assembly, and thermal caramelization of maltoheptaose-conjugated polycaprolactones leading to spherical, cylindrical, and lamellar morphologies. Macromolecules 46(22):8932–8940CrossRef
19.
Zurück zum Zitat Kumari A, Yadav SK, Yadav SC (2010) Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf B-Biointerfaces 75(1):1–18CrossRef Kumari A, Yadav SK, Yadav SC (2010) Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf B-Biointerfaces 75(1):1–18CrossRef
20.
Zurück zum Zitat Lemarchand C, Gref R, Couvreur P (2004) Polysaccharide-decorated nanoparticles. Eur J Pharm Biopharm 58(2):327–341CrossRef Lemarchand C, Gref R, Couvreur P (2004) Polysaccharide-decorated nanoparticles. Eur J Pharm Biopharm 58(2):327–341CrossRef
21.
Zurück zum Zitat Mahmoud AA, El-Feky GS, Kamel R, Awad GE (2011) Chitosan/sulfobutylether-β-cyclodextrin nanoparticles as a potential approach for ocular drug delivery. Int J Pharm 413(1–2):229–236CrossRef Mahmoud AA, El-Feky GS, Kamel R, Awad GE (2011) Chitosan/sulfobutylether-β-cyclodextrin nanoparticles as a potential approach for ocular drug delivery. Int J Pharm 413(1–2):229–236CrossRef
22.
Zurück zum Zitat Mazzarino L, Otsuka I, Halila S, Bubniak Ldos S, Mazzucco S, Santos-Silva MC, Lemos-Senna E, Borsali R (2014) Xyloglucan-block-poly(ϵ-caprolactone) copolymer nanoparticles coated with chitosan as biocompatible mucoadhesive drug delivery system. Macromol Biosci 14(5):709–719CrossRef Mazzarino L, Otsuka I, Halila S, Bubniak Ldos S, Mazzucco S, Santos-Silva MC, Lemos-Senna E, Borsali R (2014) Xyloglucan-block-poly(ϵ-caprolactone) copolymer nanoparticles coated with chitosan as biocompatible mucoadhesive drug delivery system. Macromol Biosci 14(5):709–719CrossRef
23.
Zurück zum Zitat Noronha CN, Granada AF, Carvalho SM, Lino RC, Maciel VOB, Barreto PLM (2013) Optimization of α-tocopherol loaded nanocapsules by the nanoprecipitation method. Ind Crop Prod 50:896–903CrossRef Noronha CN, Granada AF, Carvalho SM, Lino RC, Maciel VOB, Barreto PLM (2013) Optimization of α-tocopherol loaded nanocapsules by the nanoprecipitation method. Ind Crop Prod 50:896–903CrossRef
24.
Zurück zum Zitat O'reilly RK (2007) Spherical polymer micelles: nanosized reaction vessels? Philos Trans R Soc A Math Phys Eng Sci 365(1861):2863–2878CrossRef O'reilly RK (2007) Spherical polymer micelles: nanosized reaction vessels? Philos Trans R Soc A Math Phys Eng Sci 365(1861):2863–2878CrossRef
25.
Zurück zum Zitat Otsuka I, Fuchise K, Halila S, Fort S, Aissou K, Pignot-Paintrand I, Chen Y, Narumi A, Kakuchi T, Borsali R (2010) Thermoresponsive vesicular morphologies obtained by self-assemblies of hybrid oligosaccharide-block-poly(N-isopropylacrylamide) copolymer systems. Langmuir 26(4):2325–2332CrossRef Otsuka I, Fuchise K, Halila S, Fort S, Aissou K, Pignot-Paintrand I, Chen Y, Narumi A, Kakuchi T, Borsali R (2010) Thermoresponsive vesicular morphologies obtained by self-assemblies of hybrid oligosaccharide-block-poly(N-isopropylacrylamide) copolymer systems. Langmuir 26(4):2325–2332CrossRef
26.
Zurück zum Zitat Otsuka I, Isono T, Rochas C, Halila S, Fort S, Satoh T, Kakuchi T, Borsali R (2012a) 10 nm scale cylinder-cubic phase transition induced by caramelization in sugar-based block copolymers. ACS Macro Lett 1(12):1379–1382CrossRef Otsuka I, Isono T, Rochas C, Halila S, Fort S, Satoh T, Kakuchi T, Borsali R (2012a) 10 nm scale cylinder-cubic phase transition induced by caramelization in sugar-based block copolymers. ACS Macro Lett 1(12):1379–1382CrossRef
27.
Zurück zum Zitat Otsuka I, Travelet C, Halila S, Fort S, Pignot-Paintrand I, Narumi A, Borsali R (2012b) Thermoresponsive self-assemblies of cyclic and branched oligosaccharide-block-poly(N-isopropylacrylamide) diblock copolymers into nanoparticles. Biomacromolecules 13(5):1458–1465CrossRef Otsuka I, Travelet C, Halila S, Fort S, Pignot-Paintrand I, Narumi A, Borsali R (2012b) Thermoresponsive self-assemblies of cyclic and branched oligosaccharide-block-poly(N-isopropylacrylamide) diblock copolymers into nanoparticles. Biomacromolecules 13(5):1458–1465CrossRef
28.
Zurück zum Zitat Otsuka I, Osaka M, Sakai Y, Travelet C, Putaux JL, Borsali R (2013a) Self-assembly of maltoheptaose-block-polystyrene into micellar nanoparticles and encapsulation of gold nanoparticles. Langmuir 29(49):15224–15230CrossRef Otsuka I, Osaka M, Sakai Y, Travelet C, Putaux JL, Borsali R (2013a) Self-assembly of maltoheptaose-block-polystyrene into micellar nanoparticles and encapsulation of gold nanoparticles. Langmuir 29(49):15224–15230CrossRef
29.
Zurück zum Zitat Otsuka I, Tallegas S, Sakai Y, Rochas C, Halila S, Fort S, Bsiesy A, Baron T, Borsali R (2013b) Control of 10 nm scale cylinder orientation in self-organized sugar-based block copolymer thin films. Nano 5(7):2637–2641 Otsuka I, Tallegas S, Sakai Y, Rochas C, Halila S, Fort S, Bsiesy A, Baron T, Borsali R (2013b) Control of 10 nm scale cylinder orientation in self-organized sugar-based block copolymer thin films. Nano 5(7):2637–2641
30.
Zurück zum Zitat Saenger WR, Jacob J, Gessler K, Steiner T, Hoffmann D, Sanbe H, Koizumi K, Smith SM, Takaha T (1998) Structures of the common cyclodextrins and their larger analogues - beyond the doughnut. Chem Rev 98(5):1787–1802CrossRef Saenger WR, Jacob J, Gessler K, Steiner T, Hoffmann D, Sanbe H, Koizumi K, Smith SM, Takaha T (1998) Structures of the common cyclodextrins and their larger analogues - beyond the doughnut. Chem Rev 98(5):1787–1802CrossRef
31.
Zurück zum Zitat Sangster J (1997) Octanol-water partition coefficients: fundamentals and physical chemistry. Wiley, New York Sangster J (1997) Octanol-water partition coefficients: fundamentals and physical chemistry. Wiley, New York
32.
Zurück zum Zitat Schärtl W (2007) Light scattering from polymer solutions and nanoparticle dispersions. Springer Laboratory Manuals in Polymer Science, New York Schärtl W (2007) Light scattering from polymer solutions and nanoparticle dispersions. Springer Laboratory Manuals in Polymer Science, New York
33.
Zurück zum Zitat Smart T, Lomas H, Massignani M, Flores-Merino MV, Perez LR, Battaglia G (2008) Block copolymer nanostructures. NanoToday 3:38–46CrossRef Smart T, Lomas H, Massignani M, Flores-Merino MV, Perez LR, Battaglia G (2008) Block copolymer nanostructures. NanoToday 3:38–46CrossRef
34.
Zurück zum Zitat Takuya I, Otsuka I, Kondo Y, Halila S, Fort S, Rochas C, Satoh T, Borsali R, Kakuchi T (2013) Sub-10 nm nano-organization in AB2 and AB3 type miktoarm star copolymers consisting of maltoheptaose and polycaprolactone. Macromolecules 46(4):1461–1469CrossRef Takuya I, Otsuka I, Kondo Y, Halila S, Fort S, Rochas C, Satoh T, Borsali R, Kakuchi T (2013) Sub-10 nm nano-organization in AB2 and AB3 type miktoarm star copolymers consisting of maltoheptaose and polycaprolactone. Macromolecules 46(4):1461–1469CrossRef
35.
Zurück zum Zitat Uekama K (2004) Design and evaluation of cyclodextrin-based drug fomulation. Chem Pharm Bull 52(8):900–915CrossRef Uekama K (2004) Design and evaluation of cyclodextrin-based drug fomulation. Chem Pharm Bull 52(8):900–915CrossRef
36.
Zurück zum Zitat Webber SE (1998) Polymer micelles: an example of self-assembling polymers. J Phys Chem B 102(15):2618–2626CrossRef Webber SE (1998) Polymer micelles: an example of self-assembling polymers. J Phys Chem B 102(15):2618–2626CrossRef
37.
Zurück zum Zitat Zanetti-Ramos BG, Lemos-Senna E, Cramail H, Cloutet E, Borsali R, Soldi V (2008) The role of surfactant in the miniemulsion polymerization of biodegradable polyurethane nanoparticles. Mater Sci Eng C-Biomimetic Supramol Syst 28(4):526–531CrossRef Zanetti-Ramos BG, Lemos-Senna E, Cramail H, Cloutet E, Borsali R, Soldi V (2008) The role of surfactant in the miniemulsion polymerization of biodegradable polyurethane nanoparticles. Mater Sci Eng C-Biomimetic Supramol Syst 28(4):526–531CrossRef
38.
Zurück zum Zitat Zhao Y, Liang H, Wang S, Wu C (2001) Self-assembly of poly(caprolactone-b-ethylene oxide-b-caprolactone) via a microphase inversion in water. J Phys Chem B 105(4):848–851CrossRef Zhao Y, Liang H, Wang S, Wu C (2001) Self-assembly of poly(caprolactone-b-ethylene oxide-b-caprolactone) via a microphase inversion in water. J Phys Chem B 105(4):848–851CrossRef
Metadaten
Titel
Novel hybrid block copolymer nanocarrier systems to load lipophilic drugs prepared by microphase inversion method
verfasst von
Andrea Granada
Issei Otsuka
Thiago Caon
Marcos Antonio Segatto Silva
Valdir Soldi
Redouane Borsali
Publikationsdatum
01.11.2017
Verlag
Springer Netherlands
Erschienen in
Journal of Polymer Research / Ausgabe 12/2017
Print ISSN: 1022-9760
Elektronische ISSN: 1572-8935
DOI
https://doi.org/10.1007/s10965-017-1351-z

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